US9120893B1 - Alkoxy polycarbonates, bisphenol monomers and methods of making and using the same - Google Patents
Alkoxy polycarbonates, bisphenol monomers and methods of making and using the same Download PDFInfo
- Publication number
- US9120893B1 US9120893B1 US14/265,237 US201414265237A US9120893B1 US 9120893 B1 US9120893 B1 US 9120893B1 US 201414265237 A US201414265237 A US 201414265237A US 9120893 B1 US9120893 B1 US 9120893B1
- Authority
- US
- United States
- Prior art keywords
- alkoxy
- polycarbonate
- monomer
- ortho
- bisphenol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000004417 polycarbonate Substances 0.000 title claims abstract description 304
- 229920000515 polycarbonate Polymers 0.000 title claims abstract description 281
- 239000000178 monomer Substances 0.000 title claims abstract description 195
- 125000003545 alkoxy group Chemical group 0.000 title claims abstract description 169
- 238000000034 method Methods 0.000 title claims abstract description 134
- 229930185605 Bisphenol Natural products 0.000 title claims abstract description 114
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 title claims description 56
- -1 alkoxy bisphenol Chemical compound 0.000 claims abstract description 208
- 229920000642 polymer Polymers 0.000 claims abstract description 60
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 195
- 239000003054 catalyst Substances 0.000 claims description 71
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 66
- 239000000463 material Substances 0.000 claims description 62
- 102100038595 Estrogen receptor Human genes 0.000 claims description 59
- 108010085330 Estradiol Receptors Proteins 0.000 claims description 58
- 238000000338 in vitro Methods 0.000 claims description 58
- 230000002401 inhibitory effect Effects 0.000 claims description 57
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims description 55
- 150000002576 ketones Chemical class 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 39
- 239000000654 additive Substances 0.000 claims description 38
- 239000000047 product Substances 0.000 claims description 36
- 239000007795 chemical reaction product Substances 0.000 claims description 32
- 230000000996 additive effect Effects 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 230000007062 hydrolysis Effects 0.000 claims description 30
- 238000006460 hydrolysis reaction Methods 0.000 claims description 30
- 239000003963 antioxidant agent Substances 0.000 claims description 29
- 230000003078 antioxidant effect Effects 0.000 claims description 28
- 229960001867 guaiacol Drugs 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 239000000376 reactant Substances 0.000 claims description 21
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 16
- 125000005587 carbonate group Chemical group 0.000 claims description 16
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 15
- 150000002009 diols Chemical class 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
- 239000000155 melt Substances 0.000 claims description 14
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 14
- 229910019142 PO4 Inorganic materials 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 125000000732 arylene group Chemical group 0.000 claims description 12
- 238000001125 extrusion Methods 0.000 claims description 12
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 12
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 claims description 12
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- 239000003456 ion exchange resin Substances 0.000 claims description 11
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 11
- 229910052698 phosphorus Inorganic materials 0.000 claims description 11
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 10
- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 claims description 10
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 10
- 239000011574 phosphorus Substances 0.000 claims description 10
- 238000006068 polycondensation reaction Methods 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 8
- 239000004305 biphenyl Substances 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 239000003921 oil Substances 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- OMNGOGILVBLKAS-UHFFFAOYSA-N 2-methoxyphenol Chemical compound COC1=CC=CC=C1O.COC1=CC=CC=C1O OMNGOGILVBLKAS-UHFFFAOYSA-N 0.000 claims description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 claims description 7
- 239000010452 phosphate Substances 0.000 claims description 7
- 150000003018 phosphorus compounds Chemical class 0.000 claims description 7
- 229920000728 polyester Polymers 0.000 claims description 7
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 6
- YXGOYRIWPLGGKN-UHFFFAOYSA-N 2,3-ditert-butylbenzene-1,4-diol Chemical class CC(C)(C)C1=C(O)C=CC(O)=C1C(C)(C)C YXGOYRIWPLGGKN-UHFFFAOYSA-N 0.000 claims description 6
- VESRBMGDECAMNH-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]-2,3,5,6-tetramethylphenol Chemical compound CC1=C(C(=C(C(=C1O)C)C)C(C)(C)C1=CC=C(C=C1)O)C VESRBMGDECAMNH-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 claims description 6
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 claims description 6
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 6
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 6
- 229960002479 isosorbide Drugs 0.000 claims description 6
- 239000012978 lignocellulosic material Substances 0.000 claims description 6
- 125000000962 organic group Chemical group 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 6
- BATCUENAARTUKW-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)-diphenylmethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BATCUENAARTUKW-UHFFFAOYSA-N 0.000 claims description 5
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 claims description 5
- 150000001299 aldehydes Chemical class 0.000 claims description 5
- JPWJQIKXWASNOD-UHFFFAOYSA-N cycloheptylidenecycloheptane Chemical group C1CCCCCC1=C1CCCCCC1 JPWJQIKXWASNOD-UHFFFAOYSA-N 0.000 claims description 5
- DNXDYHALMANNEJ-UHFFFAOYSA-N furan-2,3-dicarboxylic acid Chemical class OC(=O)C=1C=COC=1C(O)=O DNXDYHALMANNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000012535 impurity Substances 0.000 claims description 5
- 239000000314 lubricant Substances 0.000 claims description 5
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- 239000004014 plasticizer Substances 0.000 claims description 5
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 claims description 5
- 229920000638 styrene acrylonitrile Polymers 0.000 claims description 5
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 5
- 239000004793 Polystyrene Substances 0.000 claims description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
- 230000005540 biological transmission Effects 0.000 claims description 4
- 238000000071 blow moulding Methods 0.000 claims description 4
- 238000001746 injection moulding Methods 0.000 claims description 4
- 229920002959 polymer blend Polymers 0.000 claims description 4
- 229920002223 polystyrene Polymers 0.000 claims description 4
- 238000000197 pyrolysis Methods 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- 238000003856 thermoforming Methods 0.000 claims description 4
- 239000002699 waste material Substances 0.000 claims description 4
- 125000006686 (C1-C24) alkyl group Chemical group 0.000 claims description 3
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 3
- WAOPGHCXGUXHKF-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)-1,1-diphenylpropane-1,3-diol dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.C1(=CC=CC=C1)C(O)(C(CO)(CO)CO)C1=CC=CC=C1 WAOPGHCXGUXHKF-UHFFFAOYSA-N 0.000 claims description 3
- JINIYQLAUAUHJU-UHFFFAOYSA-N 2,3-ditert-butylbenzene-1,4-diol;phenyl phosphono hydrogen phosphate Chemical compound OP(O)(=O)OP(O)(=O)OC1=CC=CC=C1.CC(C)(C)C1=C(O)C=CC(O)=C1C(C)(C)C JINIYQLAUAUHJU-UHFFFAOYSA-N 0.000 claims description 3
- SWZKJGCNTCZEEO-UHFFFAOYSA-N O(P(=O)(OP(=O)(O)O)OC1=CC(O)=CC=C1)C1=CC=CC=C1 Chemical compound O(P(=O)(OP(=O)(O)O)OC1=CC(O)=CC=C1)C1=CC=CC=C1 SWZKJGCNTCZEEO-UHFFFAOYSA-N 0.000 claims description 3
- SEMGMKPTFIDYGI-UHFFFAOYSA-N benzene-1,4-diol;phenyl phosphono hydrogen phosphate Chemical compound OC1=CC=C(O)C=C1.OP(O)(=O)OP(O)(=O)OC1=CC=CC=C1 SEMGMKPTFIDYGI-UHFFFAOYSA-N 0.000 claims description 3
- 125000006267 biphenyl group Chemical group 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 239000003086 colorant Substances 0.000 claims description 3
- 238000000748 compression moulding Methods 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- 239000003063 flame retardant Substances 0.000 claims description 3
- GLQSJLXTVROKNU-UHFFFAOYSA-N phenyl phosphono hydrogen phosphate Chemical compound OP(O)(=O)OP(O)(=O)OC1=CC=CC=C1 GLQSJLXTVROKNU-UHFFFAOYSA-N 0.000 claims description 3
- MHCIXKUPFVZFQD-UHFFFAOYSA-N phenyl phosphono hydrogen phosphate 3,3'-spirobi[1,2-dihydroindene] Chemical compound OP(O)(=O)OP(O)(=O)Oc1ccccc1.C1CC2(CCc3ccccc23)c2ccccc12 MHCIXKUPFVZFQD-UHFFFAOYSA-N 0.000 claims description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 claims description 3
- 238000005245 sintering Methods 0.000 claims description 3
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 150000003624 transition metals Chemical class 0.000 claims description 3
- 125000005270 trialkylamine group Chemical group 0.000 claims description 3
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 claims description 3
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- BJRMDQLATQGMCQ-UHFFFAOYSA-N C=C.C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 Chemical compound C=C.C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 BJRMDQLATQGMCQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000004609 Impact Modifier Substances 0.000 claims description 2
- 229920009204 Methacrylate-butadiene-styrene Polymers 0.000 claims description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004697 Polyetherimide Substances 0.000 claims description 2
- 229920000147 Styrene maleic anhydride Polymers 0.000 claims description 2
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 claims description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 2
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 claims description 2
- LKAVYBZHOYOUSX-UHFFFAOYSA-N buta-1,3-diene;2-methylprop-2-enoic acid;styrene Chemical compound C=CC=C.CC(=C)C(O)=O.C=CC1=CC=CC=C1 LKAVYBZHOYOUSX-UHFFFAOYSA-N 0.000 claims description 2
- FACXGONDLDSNOE-UHFFFAOYSA-N buta-1,3-diene;styrene Chemical compound C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 FACXGONDLDSNOE-UHFFFAOYSA-N 0.000 claims description 2
- 238000010924 continuous production Methods 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 229920001601 polyetherimide Polymers 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims description 2
- 239000011227 reinforcement additive Substances 0.000 claims description 2
- 239000011973 solid acid Substances 0.000 claims description 2
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 claims description 2
- 229920001935 styrene-ethylene-butadiene-styrene Polymers 0.000 claims description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 238000010923 batch production Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 88
- 230000000670 limiting effect Effects 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 description 44
- 235000006708 antioxidants Nutrition 0.000 description 28
- 125000004432 carbon atom Chemical group C* 0.000 description 28
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 27
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 26
- 239000002253 acid Substances 0.000 description 26
- 230000027455 binding Effects 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 229930182833 estradiol Natural products 0.000 description 20
- 229960005309 estradiol Drugs 0.000 description 20
- 238000006116 polymerization reaction Methods 0.000 description 20
- 150000003254 radicals Chemical class 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000003795 chemical substances by application Substances 0.000 description 17
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000003017 thermal stabilizer Substances 0.000 description 14
- 229920001577 copolymer Polymers 0.000 description 13
- 229920001169 thermoplastic Polymers 0.000 description 12
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 11
- 239000007857 degradation product Substances 0.000 description 11
- 238000005227 gel permeation chromatography Methods 0.000 description 11
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- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000004416 thermosoftening plastic Substances 0.000 description 11
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 10
- 125000004122 cyclic group Chemical group 0.000 description 10
- 235000021317 phosphate Nutrition 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 238000005809 transesterification reaction Methods 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 230000003301 hydrolyzing effect Effects 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical group [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 238000002411 thermogravimetry Methods 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 0 [2*]OC1=CC(CC2=CC([1*]O)=C(O)C=C2)=CC=C1O Chemical compound [2*]OC1=CC(CC2=CC([1*]O)=C(O)C=C2)=CC=C1O 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 6
- 239000012620 biological material Substances 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 238000006731 degradation reaction Methods 0.000 description 6
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 6
- 229920002313 fluoropolymer Polymers 0.000 description 6
- 239000004811 fluoropolymer Substances 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 239000003444 phase transfer catalyst Substances 0.000 description 6
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 6
- 239000004810 polytetrafluoroethylene Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 5
- 238000012695 Interfacial polymerization Methods 0.000 description 5
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical class [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
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- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RHFUXPCCELGMFC-UHFFFAOYSA-N n-(6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl)-n-phenylmethoxyacetamide Chemical compound OC1C(C)(C)OC2=CC=C(C#N)C=C2C1N(C(=O)C)OCC1=CC=CC=C1 RHFUXPCCELGMFC-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- OHFCLJNYYRPINY-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butylphenyl)-2-hydroxypropanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(O)CC1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1 OHFCLJNYYRPINY-UHFFFAOYSA-N 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- LGOPTUPXVVNJFH-UHFFFAOYSA-N pentadecanethioic s-acid Chemical compound CCCCCCCCCCCCCCC(O)=S LGOPTUPXVVNJFH-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 1
- 229920013639 polyalphaolefin Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005606 polypropylene copolymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- GHKGUEZUGFJUEJ-UHFFFAOYSA-M potassium;4-methylbenzenesulfonate Chemical compound [K+].CC1=CC=C(S([O-])(=O)=O)C=C1 GHKGUEZUGFJUEJ-UHFFFAOYSA-M 0.000 description 1
- XWIJIXWOZCRYEL-UHFFFAOYSA-M potassium;methanesulfonate Chemical compound [K+].CS([O-])(=O)=O XWIJIXWOZCRYEL-UHFFFAOYSA-M 0.000 description 1
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 229910052705 radium Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000001175 rotational moulding Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- KVCGISUBCHHTDD-UHFFFAOYSA-M sodium;4-methylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1 KVCGISUBCHHTDD-UHFFFAOYSA-M 0.000 description 1
- KKVTYAVXTDIPAP-UHFFFAOYSA-M sodium;methanesulfonate Chemical compound [Na+].CS([O-])(=O)=O KKVTYAVXTDIPAP-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 239000008117 stearic acid Chemical class 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 239000011145 styrene acrylonitrile resin Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 description 1
- MCZDHTKJGDCTAE-UHFFFAOYSA-M tetrabutylazanium;acetate Chemical compound CC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MCZDHTKJGDCTAE-UHFFFAOYSA-M 0.000 description 1
- GFZMLBWMGBLIDI-UHFFFAOYSA-M tetrabutylphosphanium;acetate Chemical compound CC([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC GFZMLBWMGBLIDI-UHFFFAOYSA-M 0.000 description 1
- DFQPZDGUFQJANM-UHFFFAOYSA-M tetrabutylphosphanium;hydroxide Chemical compound [OH-].CCCC[P+](CCCC)(CCCC)CCCC DFQPZDGUFQJANM-UHFFFAOYSA-M 0.000 description 1
- SFORWUUPTGSYHA-UHFFFAOYSA-M tetrabutylphosphanium;phenoxide Chemical compound [O-]C1=CC=CC=C1.CCCC[P+](CCCC)(CCCC)CCCC SFORWUUPTGSYHA-UHFFFAOYSA-M 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000007944 thiolates Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- QVOFCQBZXGLNAA-UHFFFAOYSA-M tributyl(methyl)azanium;hydroxide Chemical compound [OH-].CCCC[N+](C)(CCCC)CCCC QVOFCQBZXGLNAA-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- NJMOHBDCGXJLNJ-UHFFFAOYSA-N trimellitic anhydride chloride Chemical compound ClC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 NJMOHBDCGXJLNJ-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- YJLVKRVGSARISS-UHFFFAOYSA-N tris(2,6-dimethylphenyl) phosphite Chemical compound CC1=CC=CC(C)=C1OP(OC=1C(=CC=CC=1C)C)OC1=C(C)C=CC=C1C YJLVKRVGSARISS-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- LKCUKVWRIAZXDU-UHFFFAOYSA-L zinc;hydron;phosphate Chemical compound [Zn+2].OP([O-])([O-])=O LKCUKVWRIAZXDU-UHFFFAOYSA-L 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/22—General preparatory processes using carbonyl halides
- C08G64/24—General preparatory processes using carbonyl halides and phenols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
- C08K5/526—Esters of phosphorous acids, e.g. of H3PO3 with hydroxyaryl compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
Abstract
Description
regardless of whether 2,4-dihydroxyphenyl is used to prepare the compound. In some aspects the radical (for example an alkyl) can be further modified (i.e., substituted alkyl) by having bonded thereto one or more “substituent radicals.” The number of atoms in a given radical is not critical to the present invention unless it is indicated to the contrary elsewhere herein.
where Mi is the molecular weight of a chain and Ni is the number of chains of that molecular weight. Mn can be determined for polymers, e.g., polycarbonate polymers, by methods well known to a person having ordinary skill in the art using molecular weight standards, e.g. polycarbonate standards or polystyrene standards, preferably certified or traceable molecular weight standards.
where Mi is the molecular weight of a chain and Ni is the number of chains of that molecular weight. Compared to Mn, Mw takes into account the molecular weight of a given chain in determining contributions to the molecular weight average. Thus, the greater the molecular weight of a given chain, the more the chain contributes to the Mw. Mw can be determined for polymers, e.g. polycarbonate polymers, by methods well known to a person having ordinary skill in the art using molecular weight standards, e.g. polycarbonate standards or polystyrene standards, preferably certified or traceable molecular weight standards.
BisA can also be referred to by the
wherein each of R1 and R2 is independently selected from C1-C26 alkyl and C6-C26 alkaryl; and X is alkyl or arylalkyl. In yet further aspects, X is a bridging group connecting the two hydroxy-substituted aromatic groups, where the bridging group and the hydroxy substituent of each C6 arylene group are disposed meta, or para (specifically para) to each other on the C6 arylene group, for example, and without limitation, a single bond, —O—, —S—, —S(O)—, —S(O)2—, —C(O)—, or a C3-C18 organic group, which can be cyclic or acyclic, aromatic or non-aromatic, and can further comprise heteroatoms such as halogens, oxygen, nitrogen, sulfur, silicon, or phosphorous. For example, according to still further aspects, X can be a substituted or unsubstituted C3-C12 cycloalkylidene; a C3-C12 alkylidene of the formula —C(Rc)(Rd)— wherein Rc and Rd are each independently hydrogen, C1-C12 alkyl, C1-C12 cycloalkyl, C7-C12 arylalkyl. In yet further aspects, each of R1 and R2 is independently selected from methyl, ethyl, propyl, octyl, isooctyl, benzyl, ethyl phenyl, butyl phenyl, propyl diphenyl, and cyclohexyl phenyl. In even further aspects, each of R1 and R2 is methyl. In even further aspects, X is selected from methylene, cyclohexyl-methylene, 2-[2.2.1]-bicycloheptylidene, ethylidene, isopropylidene, neopentylidene, cyclohexylidene, cyclopentadecylidene, cyclododecylidene, and adamantylidene. In other aspects, X is selected from ethylidene, isopropylidene, isobutylidene neopentylidene, cyclohexylidene, alkyl substituted cyclohexylidene, aryl, cyclopentadecylidene, cyclododecylidene, sulfo, oxo, and bicycloheptylidene; and wherein each of R1 and R2 is independently selected from methyl, ethylidene, propylidene, butylidene, benzyl, phenyl, C1 to C4 alkyl phenyl, and cyclohexylidene.
-A1-Y1-A2- (2),
HO-A1-Y1-A2-OH (3),
wherein each of R1 and R2 is independently selected from C1-C26 alkyl and C6-C26 alkaryl; and X is alkyl or aralkyl. In still further aspects, X can be a C3 to C16 hydrocarbon including, but not limited to cyclic hydrocarbons. In yet further aspects, each of R1 and R2 is independently selected from methyl, ethyl, propyl, octyl, isooctyl, benzyl, ethyl phenyl, butyl phenyl, propyl diphenyl, and cyclohexyl phenyl. In even further aspects, each of R1 and R2 is methyl. In even further aspects, X is selected from methylene, cyclohexyl-methylene, 2-[2.2.1]-bicycloheptylidene, ethylidene, isopropylidene, neopentylidene, cyclohexylidene, cyclopentadecylidene, cyclododecylidene, and adamantylidene. In other aspects, X is selected from ethylidene, isopropylidene, isobutylidene neopentylidene, cyclohexylidene, alkyl substituted cyclohexylidene, aryl, cyclopentadecylidene, cyclododecylidene, sulfo, oxo, and bicycloheptylidene; and wherein each of R1 and R2 is independently selected from methyl, ethylidene, propylidene, butylidene, benzyl, phenyl, C1 to C4 alkyl phenyl, and cyclohexylidene
HmPtOn,
wherein each of R1 and R2 is independently selected from C1-C26 alkyl and C6-C26 alkaryl; wherein X is a bridging group connecting the two hydroxy-substituted aromatic groups selected from —O—, —S—, —S(O)—, —S(O)2—, —C(O)—, or a C3-18 organic group; and wherein the bridging group and the hydroxy substituent of each C6 arylene group are disposed meta, or para to each other on the arylene group bearing the phenolic (OH) functionality.
wherein each of R1 and R2 is independently selected from C1-C26 alkyl and C6-C26 alkaryl; wherein X is a bridging group connecting the two hydroxy-substituted aromatic groups selected from —O—, —S—, —S(O)—, —S(O)2—, —C(O)—, or a C3-18 organic group; and wherein the bridging group and the hydroxy substituent of each C6 arylene group are disposed meta, or para to each other on the arylene group bearing the phenolic (OH) functionality.
TABLE 1 | |||
Ex. | Compounds | IC50 rhER (α) | IC50 rhER (β1) |
A | 17b-estradiol control | 1.0 × E−9 | 8.2 × E−9 |
B | p-Cumyl Phenol (CAS# 599-64-4) | 1.4 × E−4 | 9.8 × E−6 |
C | Dihydroxy Diphenyl Ether | 6.0 × E−5 | 1.4 × E−5 |
(CAS# 1965-09-9) | |||
D | Bisphenol Acetophenone | 1.2 × E−5 | 1.4 × E−6 |
(CAS# 1571-75-1) | |||
E | Dimethyl Acetophenone Bisphenol | 4.8 × E−6 | 3.5 × E−6 |
(CAS# 4754-63-6) | |||
F | Diphenolic Acid Methyl Ester | 1.9 × E−5 | 1.1 × E−5 |
(CAS# 7297-85-0) | |||
1 | 4,4′ (2,2′-isoPropylidene)-Bis(ortho | >2.5 × E−4 | >2.5 × E−4 |
Methoxy)Phenol (PBMP) | |||
2 | Phenol (CAS# 108-95-2) | >2.5 × E−4 | >2.5 × E−4 |
IC50 is the conc. of the candidate | >2.5 × E4 compounds did not | |
that displaces 50% of the | compete to the extent of 50% | |
radioactive ligand from the | with radiolabeled 17B-estradiol at | |
rhER cells | the highest conc. (250,000 nM) | |
tested, no IC50 can be determined | ||
TABLE 2 | |||
Guaiacol-PC | BPA- |
||
6% wt loss 158° C. | 3% wt loss 175° C. | ||
10% wt. loss 406° C. | 10% wt. loss 490° C. | ||
max wt. loss 436° C. | max wt. loss 530° C. | ||
79% wt. loss 500° C. | 70% wt. loss 570° C. | ||
91% total wt loss N2 | 80% total wt loss N2 | ||
TABLE 3 | |||||
Absorbance | PBMP-PC | BPA-PC | Shift (nm) | ||
0.05 | 292 | 308 | 16 | ||
0.1 | 299 | 285 | 14 | ||
0.5 | 293 | 279 | 14 | ||
1.0 | 291 | 277 | 14 | ||
peak | 252 | 243/252 | — | ||
TABLE 4 | ||||
Day | PC Cast Film | PBMP PC | PC w/ | |
Molecular |
0 | 30496 | 23111 | 29081 | |
Weight | 2 | 29662 | 22205 | 26268 |
(Mw) | 4 | 28178 | 21149 | 23487 |
8 | 26667 | 19328 | 14594 | |
11 | 25840 | 18314 | 11166 | |
|
0 | 100 | 100 | 100 |
Retention | 2 | 97.1 | 96.1 | 90.3 |
(Mw) | 4 | 92.3 | 91.5 | 80.8 |
8 | 87.4 | 83.6 | 50.2 | |
11 | 84.7 | 79.2 | 38.4 | |
Claims (48)
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US14/265,237 US9120893B1 (en) | 2014-04-29 | 2014-04-29 | Alkoxy polycarbonates, bisphenol monomers and methods of making and using the same |
CN201580031210.XA CN106604949A (en) | 2014-04-29 | 2015-04-29 | Alkoxy polycarbonates, bisphenol monomers and methods of making and using same |
EP15728225.2A EP3137444A2 (en) | 2014-04-29 | 2015-04-29 | Alkoxy polycarbonates, bisphenol monomers and methods of making and using the same |
PCT/US2015/028185 WO2015168225A2 (en) | 2014-04-29 | 2015-04-29 | Alkoxy polycarbonates, bisphenol monomers and methods of making and using the same |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2019002503A1 (en) * | 2017-06-29 | 2019-01-03 | Katholieke Universiteit Leuven | Preparation process of ortho alkoxy bisphenol monomers |
US20200369597A1 (en) * | 2014-12-23 | 2020-11-26 | Rutgers, The State University Of New Jersey | Polymeric biomaterials derived from phenolic monomers and their medical uses |
CN113402704A (en) * | 2021-07-09 | 2021-09-17 | 万华化学集团股份有限公司 | Polycarbonate copolymer and preparation method and application thereof |
US20210309818A1 (en) * | 2020-04-06 | 2021-10-07 | Rensselaer Polytechnic Institute | Methods of making anion exchange membrane via simultaneous post-functionalization and crosslinking of epoxidized sbs |
US11306221B2 (en) | 2019-05-07 | 2022-04-19 | Shpp Global Technologies B.V. | Additively manufactured article and method |
US11834577B2 (en) | 2018-09-26 | 2023-12-05 | Sabic Global Technologies B.V. | Polycarbonate composition and associated article and method of additive manufacturing |
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CN109912646B (en) * | 2019-03-08 | 2021-02-09 | 南通江山农药化工股份有限公司 | Preparation method of bisphenol A-bis (diphenyl phosphate) flame retardant |
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WO2023208724A1 (en) | 2022-04-27 | 2023-11-02 | Covestro Deutschland Ag | Polycarbonate cocondensate with phenolic building blocks |
WO2023208723A1 (en) | 2022-04-27 | 2023-11-02 | Covestro Deutschland Ag | Polycarbonate with phenolic building blocks and low chlorine content |
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Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3635895A (en) | 1965-09-01 | 1972-01-18 | Gen Electric | Process for preparing thermoplastic polycarbonates |
US4001184A (en) | 1975-03-31 | 1977-01-04 | General Electric Company | Process for preparing a branched polycarbonate |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7666972B2 (en) | 2007-10-18 | 2010-02-23 | SABIC Innovative Plastics IP B., V. | Isosorbide-based polycarbonates, method of making, and articles formed therefrom |
US8247619B2 (en) * | 2008-12-11 | 2012-08-21 | Sabic Innovative Plastics Ip B.V. | BPA and polycarbonate made from renewable materials |
US8669315B2 (en) * | 2011-08-22 | 2014-03-11 | Sabic Innovative Plastics Ip B.V. | Polycarbonate compositions and methods for the manufacture and use thereof |
-
2014
- 2014-04-29 US US14/265,237 patent/US9120893B1/en not_active Expired - Fee Related
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2015
- 2015-04-29 EP EP15728225.2A patent/EP3137444A2/en not_active Withdrawn
- 2015-04-29 WO PCT/US2015/028185 patent/WO2015168225A2/en active Application Filing
- 2015-04-29 CN CN201580031210.XA patent/CN106604949A/en active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3635895A (en) | 1965-09-01 | 1972-01-18 | Gen Electric | Process for preparing thermoplastic polycarbonates |
US4001184A (en) | 1975-03-31 | 1977-01-04 | General Electric Company | Process for preparing a branched polycarbonate |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20200369597A1 (en) * | 2014-12-23 | 2020-11-26 | Rutgers, The State University Of New Jersey | Polymeric biomaterials derived from phenolic monomers and their medical uses |
US11649203B2 (en) * | 2014-12-23 | 2023-05-16 | Rutgers, The State University Of New Jersey | Polymeric biomaterials derived from phenolic monomers and their medical uses |
WO2019002503A1 (en) * | 2017-06-29 | 2019-01-03 | Katholieke Universiteit Leuven | Preparation process of ortho alkoxy bisphenol monomers |
CN110809570A (en) * | 2017-06-29 | 2020-02-18 | 鲁汶天主教大学 | Preparation method of ortho-alkoxy bisphenol monomer |
US11414519B2 (en) | 2017-06-29 | 2022-08-16 | Katholieke Universiteit Leuven | Ortho alkoxy bisphenol monomers |
CN110809570B (en) * | 2017-06-29 | 2023-06-23 | 鲁汶天主教大学 | Preparation method of ortho-alkoxy bisphenol monomer |
US11834577B2 (en) | 2018-09-26 | 2023-12-05 | Sabic Global Technologies B.V. | Polycarbonate composition and associated article and method of additive manufacturing |
US11306221B2 (en) | 2019-05-07 | 2022-04-19 | Shpp Global Technologies B.V. | Additively manufactured article and method |
US20210309818A1 (en) * | 2020-04-06 | 2021-10-07 | Rensselaer Polytechnic Institute | Methods of making anion exchange membrane via simultaneous post-functionalization and crosslinking of epoxidized sbs |
CN113402704A (en) * | 2021-07-09 | 2021-09-17 | 万华化学集团股份有限公司 | Polycarbonate copolymer and preparation method and application thereof |
Also Published As
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CN106604949A (en) | 2017-04-26 |
EP3137444A2 (en) | 2017-03-08 |
WO2015168225A2 (en) | 2015-11-05 |
WO2015168225A3 (en) | 2016-02-25 |
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